Philosophy has not enjoyed a prominent place in current education movements aimed at strengthening civic engagement and promoting deliberative democracy. This paper provides a brief overview of the history of democracy and philosophy that demonstrates their long but troubled relationship. We argue that the history of Western philosophy provides a much overlooked foundational role in deliberative democracy that must be understood if we are to educate citizens. Furthermore, we argue that philosophy’s central contribution to the contemporary understanding and practice of deliberative democracy is its fostering of the critique of assumptions. We conclude the article with specific pedagogic recommendations that can bring philosophy and deliberative democracy to life for our students both in and beyond the classroom.